The Rev. Elias Brewster Hillard was the minister of the big white First Congregational Church of Plymouth. A member of the New England intelligentsia, he had acquired a fine education at Andover Academy and Yale University, where he graduated with the class of 1848. His thinking was liberal, learned, and open-minded, particularly about the education of his daughters. He was also curious, candid, excitable, and courageous; even as an old man he had “vividness and aliveness,” remembered his grandson, poet Archibald MacLeish. The minister liked to tell his children stories about their ancestors, Puritans who had sailed from England in the early 1600s. There was the tale of great-grandparents captured by Indians, and one about their grandfather Moses, an enterprising ship’s captain who attempted to smuggle Napoleon out of France. In his spare time Elias wrote a book about four forgotten Connecticut heroes of the American Revolution.
When the young minister was the principal of a private school in Southington, Connecticut, he met his future wife, Julia Whittlesey, a student there. The daughter of a Yale-educated judge who had moved to Cleveland, Ohio, Julia was sent back East to finish her schooling, and she received what was considered the best possible education for a female in her day. Julia was diminutive and delicate with big, bright, brown eyes and dark hair. Besides being very feminine and lovely looking, she was possessed of a “sweet selflessness” and “charm and inward grace,” according to this grandson. When she became the mother of a large family, she was also firm, frugal, humorous, and extremely organized. Despite her practical nature, she also had an interest in spiritualism. The couple was well matched. “I can see Elias flying off on tangents and Julia holding onto his coat-tails,” said Mary Robbins Whittlesey, Julia’s older sister, for whom her daughter Mary was named.
The couple’s eldest child, Martha, born in 1856, went to Vassar College, which had opened its doors when she was nine. Her college tuition was paid for by the estate of a tall, aristocratic, and emotionally disturbed aunt who lived with the Hillards, a woman who suffered from what was called “insanity of the will.” After teaching mathematics at Vassar, Martha became principle of Rockford Seminary in Illinois until she married Andrew MacLeish. A leader in progressive education, social reform, and missionary work, she helped Jane Addams establish Hull House and was president of the Chicago Women’s Club, among many other activities. Frederick, born a year later, would invent typewriter parts but fail to profit from his patents. The third child, Helen, became a nurse and was a founder of a settlement house. Mary was born three years later in the summer of 1862, and the petite Emily was born four years after that. Then there was Fanny, who was mentally ill most of her life. The next child, precocious and sickly William, died at the age of twenty. Another son, Arthur, lived only a year. The youngest and ninth child was John, born when Mary was a teenager, who became almost like a son to her.
The Hillards raised their children based on the theories in Horace Bushnell’s Christian Nurture, which was a more affectionate approach to childrearing than the strict Puritan way; years later, however, when a young man remarked to Mary that “one hardly dares to be too happy,” she asked him with surprise, “have you got that in your background, too?” Martha later portrayed the Hillards as a happy, if financially strapped, family. Their religious expression was “simple, sincere, and beautiful,” and the children were instilled with the highest ideals. Mary was especially idealistic and wanted to become a missionary in China. In the evenings their father would read aloud Dickens, Stowe, and other novelists, while Julia and their daughters would sit around a large table doing needlework. Elias also enjoyed taking his children picnicking and camping. When he went about his parish in a sleigh or horse and buggy, he liked to take young Mary with him; she later said that she had noticed and remembered everything, like the differences in intellect and personality among his parishioners.
The Hillard family around 1894. From left: Emily, Martha (Ishbel MacLeish in lap), Elias Brewster Hillard, Mary, John, Helen, Archibald MacLeish, Julia Whittlesey Hillard, Frederick, and Fanny. CONNECTICUT HISTORICAL SOCIETY.
At the time Mary was born, on June 14, 1862, in the Connecticut village of Kensington, her father was deeply upset by the outbreak of the Civil War the year before. Inheriting her mother’s dark eyes, she would also acquire, in her eldest sister’s opinion, her mother’s take-charge manner, sense of spirituality, gift for organization, and strong belief in right and wrong. When she was a teenager, a classmate described her as “very tall, angular, almost ungainly … [but with a] directness, a dashing quickness of motion, [an] entire absence of self-consciousness and great dignity … Plain of face she may have been, dark olive and even sallow in coloring, but a face which lighted up radiantly and which was redeemed by the deep-set, very dark, very penetrating eyes—sympathetic often, quizzical oftener and with a look so far away at times that she was even then thought quite mystic and unsearchable.” This classmate, Martha Coffin, also went on to say that “there was infinite pathos” in Mary’s eyes, orbs that “were always darkened by deep circling shadows”; some friends even “called her sad-eyed.” The classmate also remembered “the fine modeling of the head, that something quite lovely about the brow and temples.” Mary grew to be one of the tallest members of her family as well as the most attractive of the clan, according to a family photograph taken around 1894, when she was thirty-two. In this photograph she is the most stylishly dressed among her dark-garbed parents and siblings, wearing a handsome light-colored suit and a dark high-necked blouse. Sitting near the center of the group, she exudes such a strong force of personality that she eclipses everyone else, even her brilliant older sisters.
After attending the local schoolhouse in Plymouth, Mary followed her sister Helen to the Collegiate Institute for Young Ladies in Waterbury, a school run by the Episcopal Church and renamed St. Margaret’s School for Girls when Mary was thirteen. Uncle Moses Hillard, a bachelor, helped with the tuition. When the headmaster of St. Margaret’s, the Rev. Francis Thayer Russell, realized that high-spirited Mary was not settling down to study, he suggested to her parents that she might do better elsewhere. At the age of eighteen her parents enrolled her in Abbott Academy, a girl’s school on a hill in Andover, Massachusetts, where she came under the influence of the elderly, authoritative headmistress, Philena McKeen, a husky-voiced woman with ringlets on both sides of her face. Mary was expected to earn her tuition, so she ran the supply shop and led a gymnastics class. She admired Miss McKeen, and a number of her later educational practices—quiet Sabbaths and simplicity of dress—became traditions at Westover. In her studies, Mary was fair in algebra and Latin but poor in French and German as well as in music and drawing. What interested her intensely were the ideas inherent in the study of history: the history of art, the history of religion, the history of linguistics, and the history of England. She also read voraciously on her own, as she would do all her life.
From an early age she was exceptional in her gift for public speaking. When asked to recite in class, she would turn recitation into something else, “a thought and question-provoking forum,” in the words of Martha Coffin. A natural leader, she was regarded as the head of the school even before she was elected president of her class. She was also firm and opinionated. Girls who went to her for advice often got “a strong bracing up, a sound whacking” instead of sympathy, recalled this classmate, who noted that nothing dampened her high spirits. One of her friends summed her up as “the biggest tease, the one who always kept her things in perfect order, who always had time for any fun going on (mostly setting it going), made the best use of her time, worked the hardest, and had the best time of any girl in school.”
The Rev. Hillard supposedly wanted Mary to go to college like her older sisters but, for reasons that are not entirely evident, she did not wish to go. Perhaps she realized that she was not a scholar, or her certainty and independence made college appear unnecessary. In an era when differences between academies and universities were not as distinct as they are today, she stayed at Abbott for four years, until she earned her high school diploma around the time